Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides

Autores
Gudiño, Esteban Dario; Iribarren, Adolfo Marcelo; Iglesias, Luis Emilio
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Candida antarctica B lipase (CAL-B) catalysed alcoholysis of a series of peracetylated alkyl α, β-D-ribofuranosides was assayed. Methyl and ethyl 2,3-di-O-acetyl-α, β-D-ribofuranosides enriched in the α-anomer were regioselectively prepared through this enzymatic deacetylation in 33% and 43% yield, respectively, the latter being a new compound. Isopropyl 2,3,5-tri-O-acetyl-β-D-ribofuranoside gave the new isopropyl 2,3-di-O-acetyl-β-D-ribofuranoside in 24% yield. The anomeric substituent affects the regioselectivity of the reaction, since n-propyl and n-butyl α, β-D-ribofuranosides reacted without selectivity.
Fil: Gudiño, Esteban Dario. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Iribarren, Adolfo Marcelo. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Ingeniería Genética y Biología Molecular "Dr. Héctor N. Torres"; Argentina
Fil: Iglesias, Luis Emilio. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Materia
CANDIDA ANTARCTICA B LIPASE
ENZYMATIC ALCOHOLYSIS
REGIOSELECTIVITY
RIBOFURANOSIDES
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/189580
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosidesGudiño, Esteban DarioIribarren, Adolfo MarceloIglesias, Luis EmilioCANDIDA ANTARCTICA B LIPASEENZYMATIC ALCOHOLYSISREGIOSELECTIVITYRIBOFURANOSIDEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Candida antarctica B lipase (CAL-B) catalysed alcoholysis of a series of peracetylated alkyl α, β-D-ribofuranosides was assayed. Methyl and ethyl 2,3-di-O-acetyl-α, β-D-ribofuranosides enriched in the α-anomer were regioselectively prepared through this enzymatic deacetylation in 33% and 43% yield, respectively, the latter being a new compound. Isopropyl 2,3,5-tri-O-acetyl-β-D-ribofuranoside gave the new isopropyl 2,3-di-O-acetyl-β-D-ribofuranoside in 24% yield. The anomeric substituent affects the regioselectivity of the reaction, since n-propyl and n-butyl α, β-D-ribofuranosides reacted without selectivity.Fil: Gudiño, Esteban Dario. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Iribarren, Adolfo Marcelo. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Ingeniería Genética y Biología Molecular "Dr. Héctor N. Torres"; ArgentinaFil: Iglesias, Luis Emilio. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaTaylor & Francis Ltd2010-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/189580Gudiño, Esteban Dario; Iribarren, Adolfo Marcelo; Iglesias, Luis Emilio; Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides; Taylor & Francis Ltd; Biocatalysis and Biotransformation; 28; 4; 6-2010; 267-2711024-2422CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3109/10242422.2010.501105info:eu-repo/semantics/altIdentifier/url/https://www.tandfonline.com/doi/full/10.3109/10242422.2010.501105info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-12T09:34:35Zoai:ri.conicet.gov.ar:11336/189580instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-11-12 09:34:35.412CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides
title Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides
spellingShingle Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides
Gudiño, Esteban Dario
CANDIDA ANTARCTICA B LIPASE
ENZYMATIC ALCOHOLYSIS
REGIOSELECTIVITY
RIBOFURANOSIDES
title_short Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides
title_full Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides
title_fullStr Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides
title_full_unstemmed Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides
title_sort Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides
dc.creator.none.fl_str_mv Gudiño, Esteban Dario
Iribarren, Adolfo Marcelo
Iglesias, Luis Emilio
author Gudiño, Esteban Dario
author_facet Gudiño, Esteban Dario
Iribarren, Adolfo Marcelo
Iglesias, Luis Emilio
author_role author
author2 Iribarren, Adolfo Marcelo
Iglesias, Luis Emilio
author2_role author
author
dc.subject.none.fl_str_mv CANDIDA ANTARCTICA B LIPASE
ENZYMATIC ALCOHOLYSIS
REGIOSELECTIVITY
RIBOFURANOSIDES
topic CANDIDA ANTARCTICA B LIPASE
ENZYMATIC ALCOHOLYSIS
REGIOSELECTIVITY
RIBOFURANOSIDES
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Candida antarctica B lipase (CAL-B) catalysed alcoholysis of a series of peracetylated alkyl α, β-D-ribofuranosides was assayed. Methyl and ethyl 2,3-di-O-acetyl-α, β-D-ribofuranosides enriched in the α-anomer were regioselectively prepared through this enzymatic deacetylation in 33% and 43% yield, respectively, the latter being a new compound. Isopropyl 2,3,5-tri-O-acetyl-β-D-ribofuranoside gave the new isopropyl 2,3-di-O-acetyl-β-D-ribofuranoside in 24% yield. The anomeric substituent affects the regioselectivity of the reaction, since n-propyl and n-butyl α, β-D-ribofuranosides reacted without selectivity.
Fil: Gudiño, Esteban Dario. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Iribarren, Adolfo Marcelo. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Ingeniería Genética y Biología Molecular "Dr. Héctor N. Torres"; Argentina
Fil: Iglesias, Luis Emilio. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
description Candida antarctica B lipase (CAL-B) catalysed alcoholysis of a series of peracetylated alkyl α, β-D-ribofuranosides was assayed. Methyl and ethyl 2,3-di-O-acetyl-α, β-D-ribofuranosides enriched in the α-anomer were regioselectively prepared through this enzymatic deacetylation in 33% and 43% yield, respectively, the latter being a new compound. Isopropyl 2,3,5-tri-O-acetyl-β-D-ribofuranoside gave the new isopropyl 2,3-di-O-acetyl-β-D-ribofuranoside in 24% yield. The anomeric substituent affects the regioselectivity of the reaction, since n-propyl and n-butyl α, β-D-ribofuranosides reacted without selectivity.
publishDate 2010
dc.date.none.fl_str_mv 2010-06
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/189580
Gudiño, Esteban Dario; Iribarren, Adolfo Marcelo; Iglesias, Luis Emilio; Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides; Taylor & Francis Ltd; Biocatalysis and Biotransformation; 28; 4; 6-2010; 267-271
1024-2422
CONICET Digital
CONICET
url http://hdl.handle.net/11336/189580
identifier_str_mv Gudiño, Esteban Dario; Iribarren, Adolfo Marcelo; Iglesias, Luis Emilio; Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides; Taylor & Francis Ltd; Biocatalysis and Biotransformation; 28; 4; 6-2010; 267-271
1024-2422
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
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dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
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eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Taylor & Francis Ltd
publisher.none.fl_str_mv Taylor & Francis Ltd
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 12.976206

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